Dimethylformamide → Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylate

HRID 467783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467783
C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[C:12]([O:16][C:17]([N:19]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:20]1[C:21]([C:27]([O:29][CH3:30])=[O:28])=[N:22][C:23](Br)=[CH:24][N:25]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>[Cu]Br.C1C=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3O)C2=CC=1.O>[C:12]([O:16][C:17]([N:19]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:20]1[C:21]([C:27]([O:29][CH3:30])=[O:28])=[N:22][C:23]([N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:24][N:25]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 86660188Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate

Produkt 1

HCID 70098560Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylateAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11762BinolKatalysatorHCID 24593copper(I) bromideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A pre-dried flask was charged with copper(I) bromide (0.35 mg, 2.89 μmol), (R)-(+)-1,1′-bi-2-naphthol (1.66 mg, 5.78 μmol) and cesium carbonate (113 mg, 347 μmol) under argon atmosphere. DMF (0.5 ml), methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate (50 mg, 116 μmol) and pyrrolidine (14.3 μl, 174 μmol) were added and the reaction mixture was stirred at r.t. for 1.5 h. The reaction mixture was poured into water (10 ml) and extracted with ethyl acetate. The combined organic layer was washed with brine, dried, evaporated and purified by silica gel chromatography using a heptane/ethyl acetate gradient to yield the product as yellow solid (37 mg, 68%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. customdried
  4. customevaporated
  5. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d8a86a22568446cbb0ceb3e1fa1820b6
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623866B2

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